A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework

Abstract

A variety of 3-arylated di- and tetrahydro-2H-2-benz­azepin-1-ones were efficiently assembled through a sequence involving a Suzuki–Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-di­ones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.

Key words

fused-ring systems - metathesis - cross-coupling - enols - ring closure

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